


The Technicalities of Kissing

by orphan_account



Category: Supernatural
Genre: Alternate Universe - High School, First Kiss, Fluff, Kissing, M/M, One Shot, Pining Dean
Language: English
Status: Completed
Published: 2014-11-28
Updated: 2014-11-28
Packaged: 2018-02-27 07:04:49
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,500
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2683739
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account
Summary: <blockquote class="userstuff">
              <p>Castiel has a date set up with some girl - Dean can't remember her name, something starting with an M - and he'd like to be prepared for a kiss, if it comes to that. The thing is, he's never kissed anyone before. The logical decision for Dean, of course, is to take his best friend under his wing and teach him the art of kissing.</p>
            </blockquote>





	The Technicalities of Kissing

Dean's kissing Castiel in his bedroom when he starts to think about how they got there, exactly. How it happened that he got Castiel on top of him, licking into his mouth and making noises that their neighbors probably considered pornographic. He starts wondering about what really  _happened_ that made the rings appear, what led to buying an apartment and getting a stupid guinea pig. The thoughts start running through his head so fast that he gets lost, Castiel pulling away and staring at him for a moment. 

"What is it?"

"Hmm?" Dean replies, meeting Castiel's eyes. 

"You're distracted," Cas sits up, cradling the other man's face in his hands. It's something Dean loves, but he'd never admit to it. Seven years of having it, and he hasn't yet.

"No, I'm not. I just started thinking."

"That's rare."

Dean mocks an offended expression, softly punching Castiel's shoulder. "Really, though. I just... it's weird, y'know? We got here. And I don't really know how."

"Well," Cas starts, head tilting as it so often does. "I tend to believe that we started this in junior year."

"That early?"

"Junior year was the first year you kissed me. About a year after that, I realized that I wanted to spend my life with you. So yes, junior year," Cas trails a hand down Dean's face, fingertips brushing across freckle-spattered cheeks. 

"But what about anything specific? Like, what action really jump-started this?" Dean takes Castiel's hand away and brings it up, pointing to the silver ring on his finger - it's engraved with  _"I need you"_ on the inside, along with a spiraling pattern around the outside. Dean's is similar, except in gold. 

Dark hair tickles his shoulder as Cas leans down. "Meg."

Dean's eyebrows pull together in confusion, and he attempts to tilt his head down to look at the one person he loves most. The person he loves so much (but could also be  _so damn confusing)._

"Meg?"

"Yes, Meg. Don't you remember?"

"I remember that she was a total-"

"Dean."

He sighs, exasperation in his tone. "Fine, fine. No, I don't really remember. I'm getting old, things are fuzzy."

"You're twenty-four."

"That's old enough to forget things. Now, what the hell is this about Meg?"

"Well," Castiel starts, and Dean can practically hear the smile in his voice. "Let me remind you."

 

***

 

Dean waited for the doorbell to ring, attempting to study as he sat in his room. Sam was sitting on the end of his bed,  _actually_ studying, but Sam didn't have anything to worry about, unlike his brother. No, Sam was just sitting, minding his own business and reading about World War One. Dean, on the other hand, had about twenty different things to worry about. Was the room clean enough? Did he look okay? Did everything smell nice? Was he prepared to not say something stupid if there was a lull in conversation?

Yeah, Dean had stuff to worry about. Dumb stuff, but still. 

"Sammy, how do you think this looks?" 

He stood up from the bed, smoothing out the few rumples in the cloth. A simple gray t-shirt, stretching across his shoulders and stomach in a flattering way. 

"Why do you care? It's just Cas coming over, right?"

The blush heats his cheeks, and he can even feel it stretch to the tops of his ears. "Yeah."

There was a heavy silence in the room, something that Dean had been hoping to avoid. Sam could read him like a book, though, so hiding a crush on his best friend hadn't been easy. He was just so  _nervous_ around Cas now - not the bad kind, but the fluttery kind that made your head feel dizzy. Even with all the weird feelings, Dean had been able to conceal his feelings and continue on with life like everything was still completely normal. But that  _one_ mistake had made everything obvious to his brother. 

"Oh," is the only response that Dean gets. 

He shrugged it off, walking down the stairs and downing a glass of water. The whole reason Cas was even coming over was simple studying, getting prepared for the test in World History they'd have tomorrow. But reading about war tactics was so _boring_ compared to looking at Cas. 

Dean had poked fun at Castiel's staring habit since they were kids, but the truth was that he was just as bad about it. He could spend hours letting his eyes roam over Castiel's features, taking in the sharp cheekbones and pronounced profile, examining the shades of blue in his eyes and tracing the bow of his lips with his gaze. 

Three glasses of water filled his system by the time Cas rang the doorbell, textbook and binder in hand. His hair and clothes were just as messy as usual, dark brown spikes forming an almost-halo. Dean opened the door quickly, a smile gracing his features as Cas walked into the house. 

"Hello, Dean."

Castiel didn't smile as he greeted his friend.  _That_ was out of the ordinary. 

"Hey, Cas."

The two boys walked up to Dean's room, Sam giving Dean a small smirk before walking out the door. They managed to get halfway through the first chapter before Castiel shut his book and looked away. 

"Cas?" Dean's first reaction was concern, and his voice conveyed it flawlessly - the added hand on Castiel's shoulder added to the effect. 

"Meg asked me out." 

The words came out in a rush, Castiel's eyes flickering to every corner of the room before they met Dean's gaze again. He didn't look happy or excited about being asked out be a girl - he looked fucking terrified. The terror in his eyes matched the twisting in Dean's gut. 

"That's great, man!" Dean claps his hand over his friend's shoulder, putting on his widest smile and trying to feel happy for him. 

"No, Dean. It is not great." 

"Why? You got a chick to-"

"Dean, you are aware of her reputation. And while I do not judge her for what activities she chooses to engage in, I believe that I should at least make an attempt to kiss her, and I have no idea how to do that." Cas swallowed, expression pained. 

"What do you mean, you don't have any idea?"

"I have never had the occasion to kiss someone, Dean," Cas looked completely serious, voice quiet and eyes intense. 

Something clicked in Dean's head, and then this fucked-up revelation seemed to turn into a golden opportunity. He swallowed, putting on a determined face. 

"Cas."

"Yes?"

"I'm gonna teach you how to kiss."

 

***

 

"Okay, hold on. That is not how it happened." Dean could barely contain his laughter at Castiel's descriptions of how he'd looked in that moment - determined, steely, slightly constipated. 

"What? That's the truth, Dean. I was there."

"Cas, just - God. Okay, just skip ahead. What did you even say after that?"

 

***

 

Castiel stared at him for a moment, blue eyes wide. "Dean, would that not complicate our friendship considerably?"

"What? No, of course not! It's not like we'd be sexing it up in the closet or anything. I'd just give you a few lessons before your date. Simple stuff, man." Dean smiled wide, hoping that he was making this sound believable. Sure, it probably wasn't the healthiest way to deal with his emotions, but he just  _really_ wanted to be with Cas - and he couldn't. So this was second-best. 

"What would we do? How do you-"

"Alright, look. If you agree, we could even start tonight. The easiest stuff. Then we'll just... move  up in difficulty. Then you'll be prepared for anything."

Castiel averted his eyes for a moment, one hand toying with the hem of his beige sweatshirt. When he finally looked at the other boy again, he looked more at ease. Maybe even  _excited._

"Yes, Dean. That would make things with Meg far simpler."

The twisting in Dean's stomach returned, but he just shook his head slightly.  _You're doing this for Cas. He probably really DOES need help._

"Alright, Cas. We're gonna start off super simple. Studying the wars and right techniques."

"A kiss for each right question?" Castiel inquired, and that phrasing made Dean feel lightheaded. He looked so innocent there - wide eyes, head tilted ever-so-slightly.  _Damn adorable._

"Sure, Cas." 

 

***

 

"Oh, yeah - I remember that. You looked fucking cute, Cas." 

"I am aware of that. Why do you think I tilted my head so much? I could see that you found it endearing."

Dean pulls back, looking Castiel in the eye. "What? You were  _playing_ me?"

Castiel smiles, face smug. Dean thinks that the glint in his eye is gorgeous, but at the moment, he can't stand it. He leans forward, planting his lips onto Castiel's chastely. It's those soft kisses that Cas likes getting the most - gentle, warm, sweet. Just like the first.

 

***

 

"Alright, that was an easy question, Cas. Do you really want to get started on this so-"

 _"Yes,_ I do." 

Castiel lunged forward on the bed, pushing Dean back against the headboard and crowding into his space. Dean's heartbeat was flying at the close proximity, every detail in Castiel's face visible. He looked desperate, and Dean would be an idiot to not teach his friend when he had  _that_ look in his eyes. 

"You have to teach me, Dean. I cannot... I cannot do this confidently." Cas swallowed, suddenly leaning back and giving his best friend some space.

"It's okay, Cas. Just - alright. I'm gonna start off with the simplest kind, okay? Sit there and close your eyes."

Cas nodded once, closing his eyes and letting his shoulders fall slightly. Courage filled Dean's veins, blood pumping with bravery; he could do this. He could kiss him, just a soft peck against soft lips. Dean brought a hand up to cup Castiel's cheek, but thought against it when he noticed the pink flush on the other boy's cheeks. Instead, he simply leaned forward and let their lips connect. 

It wasn't earth-shattering, kissing Cas. It was nice. His lips were warm against Dean's, kind of chapped but still soft. Dean pulled back after a moment, immediately missing the contact. Castiel leaned forward, chasing the contact - the movement made warmth flood Dean's chest, a smile gracing his features as Castiel looked at him. 

"That is the simplest kind?"

"Yup. Wanna try another one?"

"Yes, please."

Dean grinned wider, pulling Cas toward him. "Alright. So the next one is kind of similar, but there's more movement. Just move your lips a little."

Castiel nodded, closing the distance between them first. His lips trailed along Dean's, sparks shifting under Dean's skin. This time, he let his hands trail up to rest on the other boy's shoulders; Dean tried not to trace the lines and contours of Castiel's back, but he couldn't help it when a warm mouth was locked against his and a body was pressed close against his chest. 

It ended too soon - Cas pulled away, a hand lingering on Dean's hip. He bit his lower lip, eyes locking with Dean's again. "Was that suitable, Dean?"

A few moments passed before Dean was capable of speech again. "Uh. Yeah, yeah - it was great, Cas. You're a natural, I guess," Dean smiled at then end of his sentence, Castiel's expression lighting up to match his friend's.

"May we try again tomorrow, Dean?"

"Yes!" Dean could hear the over-eagerness in his tone, coughing once and delivering something a little more controlled. "Yeah, yeah. Sure we can, Cas."

 

***

 

The next day, Castiel didn't even bother bringing his textbooks with him. It was Wednesday, leaving them two more days until his date with Meg.  _His date with Meg. Cas going out with Meg._ That part of the kissing arrangement was something he tried to block out. He tried not to think of how he only had a few more days of Castiel's lips against his own, just a few more days where it was acceptable to let a hand trail through his hair and over his ribs. 

"Hello, Dean." 

"Hey, Cas. So, today I was thinking we could make it a little harder, y'know? Get you started on the fun part."

Castiel tilted his head as he walked into the house, following Dean up the stairs and into his room. "Fun part? I greatly enjoyed what we did yesterday. What more is there?"

A blush crept up Dean's neck, turning around for a second to glance at his friend. "It's - um. You know, Cas."

Another confused look.

"Y'know, using more than your lips and stuff. And kinda... look, I'll show you, okay?" 

Once they made their way onto Dean's bed, the air or awkwardness returned. They couldn't really look at each other, but they couldn't  _stop_ looking at each other - glancing away, then trying to look at the other, accidentally locking gazes, and glancing away again. It continued for a good five minutes before Dean grabbed Castiel's chin and forced him to look.

"So, basically - alright. I'll do some stuff, and then you try and copy it." 

Cas nodded, face tinged pink and red. Dean nodded once, then leaned in and locked his lips to Castiel's. The same sensations before - warmth, softness, Castiel's mouth completely pliant.  _Okay, Winchester. Just open your mouth a little. The fun part._

Dean let his tongue gently trace Castiel's lower lip, the other boy shivering at the new contact. The action gave Dean more confidence, opening his mouth more and silently asking for permission to go in. Cas complied, and Dean realized that while soft, chaste kisses were sweet,  _this_ was the kind of thing he wanted every day. 

Dean explored slowly, running his tongue over the roof of Castiel's mouth and letting a hand push against his jaw for a better angle. Cas tasted sweet and sugary, almost like honey. Dean was having fun just running over the contours of Castiel's mouth, wet and hot and glorious. But the second Castiel realized things would probably be more fun if he also participated, Dean saw stars. His tongue slid against Dean's, tracing the bow of his lips and flooding Dean's mouth with that sweet flavor - it was so  _Cas._

He wrapped his hands around Dean's back, warm fingers pressing into muscle and tugging Dean closer. Castiel let a hand trail up his back, wrapping in Dean's hair and tugging just slightly; the feel of his fingers running over the short strands made Dean gasp softly, and both of the boys pulled back for air. They didn't pull far, though - they were just a few inches apart, sharing the same hot breaths as air filled their lungs. Their eyes locked together, and their lips shortly after. 

This kissing was far different from yesterday - it was frenzied and less coordinated, but the hot slide of Castiel's tongue against was making Dean lose all sense of self control. Flames flew under his skin, the air in the room feeling far too hot for this many layers of clothes. When Dean tried to take off his jacket, however, Cas pulled away. 

"Cas?"

The dark-haired boy was breathing heavily, eyes staring at the door. "I'm sorry, Dean - I'm sorry," Castiel got up quickly, darting out of the room and down the stairs. Dean didn't go after him, the shock of being left rendering him immobile. 

Sam knocked on the door, entering after he heard Dean's grumbled "come in". He sat at the foot of his brother's bed, eyes slightly concerned. 

"What happened with Cas?"

"Nothing, Sam. Go back to your room."

"Dean-"

 _"Nothing,_ Sam!"

His brother could always tell what he needed, and now was no different. Sam disappeared for all of four minutes, returning with a tub of ice cream and their boxed set of Dr. Sexy, seasons 1-4. 

 

***

 

"Why'd you run out, anyway?" Dean rubbed Castiel's lower back, question hanging in the air. 

"I got scared."

"Of what?"

Cas was silent for a moment, fiddling with the silver band between his fingers. "I saw you take off your jacket, and I was scared because I didn't want you to stop."

 

***

 

On Thursday, Dean was prepared to sit alone, in his room, and try and figure out a way to fix things with Cas. He didn't know what had happened, but he did know that whatever it was couldn't be bad enough to ruin their friendship - even if he couldn't be with him romantically, Dean still wanted to be Castiel's friend. He wasn't sure if he could ever be really happy without Cas in his life. So, he was prepared - but then all that went to hell when he heard a knock on his door. 

"Dean?"

Castiel was standing outside, wringing his hands and looking like a kicked puppy. Dean let him inside, the two sitting down in the kitchen. 

"I would like to continue our lessons, if you would allow it. I am still lacking "experience", and would greatly appreciate your assistance in this area of romance."

Dean didn't even answer; he just grabbed Castiel's collar and pulled him over the table, lips crushing together with more force than was probably necessary. They stopped after a quick moment, rushing up to Dean's room to continue. The thing about it was that once again, Cas showed him that there was more to kissing then he'd thought before. 

Castiel kissed him like he was something precious, hands cupping his face and lips placing soft kisses on his cheekbones and along his jaw. He wasn't hurried, but gentle - running his tongue lightly across Dean's lips and over the roof of his mouth, pressing against him as they leaned on the headboard. Dean let his hands tangle in Castiel's hair and run over his sides, careful to keep all clothes on and let Castiel lead him in the kiss. 

Their touches were tender and soft, some of the kisses chaste. Castiel let his mouth trail along Dean's neck, sucking lightly on his pulse point and nipping along his collarbone. Dean almost melted at the touch, settling on wrapping his arms around his friend's waist and letting Cas just  _kiss_ him. 

Castiel kept on with his ministrations, the occasional bruise marking Dean's throat, both of their mouths red and slick. Dean never wanted it to end. 

 

***

 

"Love you, Cas," Dean whispered between soft meetings of lips, tangling his fingers in his husband's hair. 

"I love you too, Dean. But I really would like to finish the story," Castiel finishes his sentence with a soft moan as Dean rolls his hips gently, fixing the other man in his bed with a glare. 

"Don't we already know? It ends up here."

"There's one more part that's important."

 

***

 

Friday came, and it was time for Castiel's date with Meg. 

Dean knew, without a doubt, that there would be no knock on his door. He settled back in front of his TV, prepared to eat his feelings and maybe watch some of his favorite Dr. Sexy episodes again. He practically had them memorized, but that didn't make the watching experience any less enjoyable. Right as he turned on the first episode of season 4, he heard a sound. 

It came again a few moments later, loud and urgent. He rushed to the door, groaning while he abandoned the remote. He opened the door quickly, about to tell whatever salesman that was waiting to get the fuck off his porch, but instead he found Castiel on his doorstep.

Cas, still dressed in his "fancy date" outfit, a nice button-down and slacks, hair sticking up from running his hands through it. He looked up at Dean with an unreadable expression, something that could have been hope or worry. 

"Cas? What are you-"

"I had to leave," His words were rushed, hands balling up in the hem of his shirt. "I couldn't stay. She kept trying to say these  _things_ to me, but I didn't care, Dean. She tried to lean over and kiss me, but I realized that - well, I..."

"Cas, what is it?" Dean pulled him inside, pushing the door shut and placing a hand on his best friend's shoulder. 

"I only wanted you to kiss me. I closed my eyes, but I just wanted you to be there but you  _weren't,_ so I left and-"

Dean kissed him. Soft and sweet, just how Cas liked. He pushed him up against the door, threading their fingers together and smiling against Castiel's lips. His mouth was warm and he kissed gently along Dean's jaw, moving a hand to wrap in the front of the other boy's shirt. 

"Dean?" Cas pulled away for a second, resting his head against Dean's shoulder. Dean could feel the soft puff of breath against his neck, and he tightened his hands around his friend - well, more than friend. 

"Yeah?"

"You're an exceptional kisser."

Dean laughed at that, tugging Cas back in and pressing their mouths together once more. 

 

***

 

"You remember now?" Castiel asks, running his hands over the freckles on Dean's shoulders. 

"Yeah, Cas," Dean murmured, smiling lazily. "I remember."

**Author's Note:**

> thanks for reading, hope you enjoyed!  
> feedback is appreciated~  
> (sorry for mistakes, haven't edited everything yet)


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